Cubs Have Reportedly Had Internal Discussions about Jon Lester and Justin Masterson

Theo Epstein and Jed Hoyer have said the front office will address the organization’s pitching needs and could add starters in the off-season if the situation, or situations, presents itself and benefit the Cubs moving forward.

The Cubs have very little financial commitments on the books for the big league team beyond this year and were able to roll over payroll from this season the front office earmarked to sign Masahiro Tanaka last off-season as well as the payroll saved by trading Jeff Samardzija and Jason Hammel to Oakland. The front office will have the financial flexibility to add veteran free agents to the big league roster as well as the prospect currency to trade for a starting pitcher if that is the route the front office thinks would benefit the Cubs in the long-term.

According to a report from the Sun-Times, the financial flexibility the Cubs will have “could mean a serious run at Red Sox free-agent ace Jon Lester or underperforming Indians ace Justin Masterson, players the Cubs have had significant internal discussions about.”

The Cubs being connected to Jon Lester and Justin Masterson was expected. The front office has a history with both starters from the years together in Boston. Theo Epstein, Jed Hoyer and Jason McLeod inherited Jon Lester while the trio selected Justin Masterson in the second round of the 2006 draft. Masterson was dealt to Cleveland, along with Bryan Price and Nick Hagadone, for Victor Martinez in July of 2009.

The Red Sox are at a turning point with Jon Lester. The 30-year old southpaw is poised to hit free agency at the end of the season after Boston and Lester have not been able to find a middle ground on an extension. Boston has five days to trade him or risk Lester walking away with only a draft pick coming back to the Sox.

While Jon Lester is putting up ace numbers and is in the conversation for an AL Cy Young award, Justin Masterson is not having a good year. Not only are his numbers bad but his velocity is down.

Jon Lester will start his new contract at 31-years old and Justin Masterson is a year younger than Lester. Long term contracts for starting pitchers are risky at best, but a risk the Cubs front office will likely take when they think the team is ready to start competing.

The Cubs were among several teams (Giants, Pirates, Braves, Orioles, Mariners and Nationals) that had top evaluators at Tropicana Field on Friday night to watch Jon Lester and David Price pitch according to Ken Rosenthal.

Jason Hammel

The Sun-Times spoke with Jason Hammel and the recently traded starter that made a lot of noise just before the deal with Oakland was announced did not shut the door on returning to the Cubs in the off-season.

Jason Hammel, like Scott Feldman, enjoyed his time with the Cubs. And like Feldman, who recommended Hammel sign with the Cubs, Hammel has put himself in line for a multi-year contract this off-season after spending four months with Chris Bosio and the Cubs.

Hammel told the Sun-Times he was hoping he had pitched well enough that the front office would not trade him. Hammel “found the sudden, jump-the-market trade tougher on him and his pregnant wife than he anticipated.”

Theo Epstein, Jed Hoyer and the front office took responsibility for the lack of communication with Hammel the day he was traded and smoothed things over with Hammel after the deal was done. According to the Sun-Times, “the Cubs tried to maintain good relations with Hammel.”